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Reaction of 2,3-dioxopyrrolo[2,1-a]iso-quinolines with binucleophiles

  • O. V. Surikova
  • A. G. MikhailovskiiEmail author
  • M. I. Vakhrin
Article

The reaction of 2,3-dioxopyrrolo[2,1-a]isoquinolines with binucleophiles such as 2-amino-4-methyl-phenol, o-aminothiophenol, and caprolactam hydrazidine proceeds with opening of the dioxopyrroline ring and is accompanied by heterocyclization to give heteroaromatic benzoxazole, benzothiazole, and 1,2,4-triazole systems. Heterocyclization does not occur in the reaction of o-hydroxybenzylamine, o-aminobenzyl alcohol, and the hydrazide of anthranilic acid; the corresponding linear N-benzylamide, benzyl ester, and diacylhydrazide products are formed.

Keywords

o-aminobenzyl alcohol 2-amino-4-methylphenol o-aminothiophenol N-benzylamide benzyl ester anthranilic acid hydrazide caprolactam hydrazidine o-hydroxybenzylamine diacyl hydrazide 5,5-dialkyl-2,3-dioxopyrrolo[2,1-a]isoquinolines benzoxazole benzothiazole and 1,2,4-triazole derivatives 

References

  1. 1.
    N. N. Polygalova and A. G. Mikhailovskii, Khim. Geterotsikl. Soedin., 1383 (2005). [Chem. Heterocycl. Comp., 41, 1178 (2005)].Google Scholar
  2. 2.
    A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., 946 (1994). [Chem. Heterocycl. Comp., 30, 818 (1994)].Google Scholar
  3. 3.
    A. G. Mikhailovskii, V. S. Shklyaev, and B. B. Aleksandrov, Khim. Geterotsikl. Soedin., 808 (1990). [Chem. Heterocycl. Comp., 26, 674 (1990)].Google Scholar
  4. 4.
    N. N. Polygalova, A. G. Mikhailovskii, E. V. Vikhareva, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 1068 (2007). [Chem. Heterocycl. Comp., 43, 900 (2007)].Google Scholar
  5. 5.
    O. V. Surikova, A. G. Mikhailovskii, N. N. Polygalova, P. G. Neifel'd, and M. I. Vakhrin, Zh. Org. Khim., 43, 1416 (2007).Google Scholar
  6. 6.
    O. V. Surikova, A. G. Mikhailovskii, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 298 (2008). [Chem. Heterocycl. Comp., 44, 231 (2008)].Google Scholar
  7. 7.
    A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., 1697 (1995). [Chem. Heterocycl. Comp., 31, 1475 (1995)].Google Scholar
  8. 8.
    A. G. Mikhailovskii, Khim. Geterotsikl. Soedin., 685 (1996). [Chem. Heterocycl. Comp., 32, 590 (1996)].Google Scholar
  9. 9.
    V. S. Shklyaev, B. B. Aleksandrov, A. G. Mikhailovskii, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., 963 (1987). [Chem. Heterocycl. Comp., 23, 790 (1987)]. cGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • O. V. Surikova
    • 1
  • A. G. Mikhailovskii
    • 1
    Email author
  • M. I. Vakhrin
    • 1
  1. 1.Perm State Pharmaceutical AcademyPermRussia

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